How Do I Create a self drawing 2D Shape?
Here is a simple way to make a drawing... draw itself:

draw a curve as your handwritten shape, or use Grease Pencil to draw your word, and then convert the drawing to a curve. See here:



Then you have (at least) two ways: 


Use a mesh to create the writing depth, through arrays (fit length) and other modifiers: curve follow, subsurf. Then animating the "fit length" array parameter you can make it draw itself...


Here's how:




Use another (curve) shape as bevel object for the first curve. Then animating the bevel "end factor" you can make it draw itself...


Like this:



This becomes a 3D writing because the bevel object is a 2D curve circle, but you can also get a 2D animated writing using a 1D curve as bevel object, like this: